Dimethylamine → HCID 9862515, compound

HRID 1377485Notes

Reaction equation

HRID 1377485 reaction equation
[CH3:1][N:2]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:10]([CH2:18][CH2:19][C:20](O)=[O:21])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[O:23].[CH3:24][NH:25][CH3:26]>ClCCl>[CH3:24][N:25]([CH3:26])[C:20](=[O:21])[CH2:19][CH2:18][C:10]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](=[O:23])[N:2]([CH3:1])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 15839869HCID 15839869, compound

Product 1

HCID 9862515HCID 9862515, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 0.9 g (2.93 mmol) of 2-methyl-1-oxo-3-phenyl-1,2-dihydroisoquinoline-4-propanoic acid in 150 ml of dichloromethane is prepared in a 500 ml round-bottomed flask placed under an argon atmosphere, 0.7 g (4.3 mmol) of N,N'-carbonyldiimidazole is added, the mixture is stirred at room temperature for 2 h, is saturated for 1 min with gaseous dimethylamine and stirring is continued for 12 h. The solvent is evaporated under reduced pressure, the residue is taken up in 200 ml of dichloromethane, 100 ml of water and 1M hydrochloric acid, the organic phase is separated, washed with water, dried over sodium sulphate and filtered and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on a column of silica gel, elution being carried out with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 70/30 and then with a 95/5 mixture of dichloromethane and methanol. After recrystallizing from a mixture of dichloromethane, methanol and acetonitrile, 0.72 g (2.15 mmol) of white solid is obtained. Melting point: 165.5°-166° C.

Workup

  1. customis prepared in a 500 ml round-bottomed flask
  2. stirringstirring
  3. waitis continued for 12 h
  4. customThe solvent is evaporated under reduced pressure
  5. custom100 ml of water and 1M hydrochloric acid, the organic phase is separated
  6. washwashed with water
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. customthe solvent is evaporated under reduced pressure
  10. customThe residue is purified by chromatography on a column of silica gel, elution
  11. additionbeing carried out with a mixture of dichloromethane and ethyl acetate ranging from 100/0 to 70/30
  12. additionwith a 95/5 mixture of dichloromethane and methanol
  13. customAfter recrystallizing from a mixture of dichloromethane, methanol and acetonitrile

Sources & evidence

ORD record
ord-bbdb5be59b8a427183af8f70fe19d58f
Source dataset
uspto-grants-1997_09
Patent number
US05665733

Reaction notes

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